Security Reminder: Tandym may send job opportunities to contacts by text message, but we will never ask you for personal information, passwords, account details, or financial details over text; we’ll never charge you money for applying for a job with Tandym; we’ll never ask you to install software; we’ll never ask you to switch to a different messaging platform like WhatsApp. If you receive any additional messages that look suspicious, please call our corporate headquarters at (212) 922-1001.
December 15, 2022 | 5 min read
How To Answer 25 Of The Most Tricky Interview Questions

Amanda

Everyone has heard those stories of tricky interview questions that are meant to trip you up; one wrong move, and you could lose the whole opportunity! When you’re preparing for an interview, the unknown is the most nerve-racking part. What is the hiring manager going to ask? Are they going to try to get me flustered? What if I can’t think of an answer, and there’s a long, awkward pause?

While you may not have full control over how your interview goes, you can ease your nerves with a little bit of preparation. When you’re confident about those tricky interview questions that may come up, it will show in your overall interview performance.

We’ve outlined the most common, most challenging interview questions—and how you can impress the hiring manager with your answers. These questions are asked frequently, but they still manage to catch the interviewee off guard. Ace your interview with this guide to the trickiest questions.

Top 25 Tricky Interview Questions

Tell me about yourself…
Why are you leaving your job?
Why were you let go?
Why do you have a gap in employment?
Why did you change career paths?
What motivates you?
How many tennis balls can you fit into a pickup truck?
What can you contribute to this company?
Why do you want to work at this company?
Why do you want this job?
Why should we hire you?
Sell me this pen.
What is your work style?
What is your management style?
What is your greatest strength?
What is your biggest weakness?
How do you handle conflict in the workplace?
What is your dream job?
Where do you see yourself in 5 years?
Are you interviewing with any other companies?
When can you start?
Do you have any questions for us?
What are your salary expectations?
What is your current salary?
Are you planning to have children?

1. Tell me about yourself…

It’s a simple question, but the answer has a million possibilities. What does the hiring manager actually want to know about you? You know you shouldn’t get too personal, but you should also show your personality a bit. Here’s how to handle this first tricky question:

  • Avoid starting with personal information
  • Highlight why your skills make you the right person for the job
  • Talk about your interests related to the role
  • Think of your answer as a story
  • Keep it short and sweet
  • Confirm if you’ve answered the question

Possible answer to “Tell me about yourself…”

“I graduated from [Insert University] with a degree in [Insert Degree]. I started my career at [Insert Company] but moved on after about a year to try something new. That’s where I really found an interest in event production. I’ve managed over 15 successful events, the most recent one being 2 months ago at my current company. I have experience finding speakers, writing talk tracks, and creating presentations for different types of in-person and virtual events. I really enjoy event planning because I work well under pressure and thrive in fast-paced environments—which is what interests me about this role. I also feel the industry is very rewarding. I am currently looking for a career change as I would like room for growth and to work for a larger, more established tech-forward firm like your company.”

Read More: Tough Interview Questions: How To Respond To “Tell Me About Yourself”

2. Why are you leaving your job?

While many job seekers in this position are likely leaving their job because they’re unhappy, you know that you can’t just say, “I don’t like my job/manager/company leadership.” It’s important to still be truthful, but respectful. Here’s a few tips:

  • Be honest
  • Be professional
  • Be succinct, but thoughtful
  • Look ahead

The most important item is to turn your answer into what you are looking for. What are you no longer getting in your current role that you would like in this role?

Possible answer to “Why are you leaving your job?”

I’ve been at my current job for some time and don’t feel there is any room for growth. I’m really interested in working on XYZ and developing my skills further. I’m ready for the next step in my career and believe this new role will be what I am looking for.

Read More: How To Answer “Why Are You Leaving Your Job?”

3. Why were you let go from your previous employer?

Whether you were laid off or fired from your previous role, this can be an uncomfortable or tricky interview question to answer. However, you are not the only person who has ever been let go from a job. An understanding hiring manager knows that lay offs are not your fault, and some people just don’t mesh with certain office cultures or managers. Here’s a few steps you can take to answer this question:

  • Come to terms with your circumstances
  • Be honest about what happened
  • Talk about what you’ve learned as a result
  • Don’t bad mouth your previous employer

Possible answer to “Why were you let go?”

“Ultimately, my work style did not mesh well with their culture. I am often used to working regular hours, while their culture would often have people working later into the night. As a result, I couldn’t meet their expectations. I did learn, however, that I can work harder than I ever thought I could, and I appreciate the bond I built with my team when we worked late together. Based on what I understand about this role, I think I should be able to meet or exceed expectations.”

Read More: How To Explain Getting Fired In An Interview

4. Why do you have a gap in employment?

Regardless of your reasoning, having a gap in employment on your resume is completely normal. However, you may be asked for an explanation in your interview. Whether you were laid off, taking a sabbatical, caring for family, or attending school, a simple answer will probably suffice. Be honest about your situation, and explain how you are prepared to transition back into work.

Possible answer to “Why do you have a gap in employment?”

“After my last role at [Company], I felt burned out. It was important to me to take a sabbatical to reconnect with myself and discover how I can prevent getting burned out in my next job. During my time off, I’ve stayed up-to-date on industry news and trends, and I’m confident I can return and hit the ground running.”

Read More: How to Address An Employment Gap On Your Resume

5. Why did you change career paths?

While this feels like it could be difficult to answer, don’t be overwhelmed! An honest answer about your career change is all the hiring manager is looking for. Here’s how to handle it:

  • Explain what led you to this decision
  • Show your passion for this new career
  • Highlight your transferable skills

Possible answer to “Why did you change career paths?”

“After years working in sales, I was no longer getting enjoyment out of the process of closing deals. After some soul-searching, I realized that I want to make an impact in a more meaningful way. Transitioning into Human Resources, I still get to do the thing I love most: build relationships and work directly with people. But instead of closing a sale, I get to help someone build their dream career. I’m so excited to use all of my sales skills and techniques in a more meaningful way.”

6. What motivates you?

This question might grind you to a halt—have you ever even thought about what motivates you to succeed in your work? Before you panic, consider these two things:

  • What do you like most about your work?
  • What kind of impact do you hope to make?

Possible answer to “What motivates you?”

“I really enjoy seeing the big picture and working to organize how we will achieve those big goals. When I know the end result, I know I am working toward something that impacts so many people beyond me, and it motivates me to work harder. Additionally, I love to plan and organize, diving into each detail that will get us across the finish line. That’s why I’m so excited about this project management opportunity.”

7. How many tennis balls can you fit into a pickup truck?

This is one example of many, many off-the-wall questions that have been asked over the years. You may not get this question specifically, but it’s important to know that this isn’t really a math problem with one right answer. The hiring manager is really looking to see how you think through a problem. Here’s how to answer this type of tricky interview question:

  • Don’t give up immediately and say it’s impossible
  • Say your entire thought process out loud
  • Ask for a pen and paper (or a calculator), if you need it

Possible answer to “How many tennis balls can you fit into a pickup truck?”

“Well, let’s say we’re using cannisters of tennis balls that come in threes. Perhaps nine cannisters make up about one cubic foot. May I use a calculator for this? In a pickup truck bed, there might be about 50 cubic feet. So, let’s say about 1,350 tennis balls, probably more if you include the front seat.”

8. What can you contribute to this company?

Beyond revenue or specific tasks of your role, the hiring manager is looking to learn a little bit more about your personality; how can you add to the culture of the company and also build on its success? To answer this effectively, you should:

  • Have a deep understanding of the company through your research
  • Connect your experience to the job description
  • Use data to back up your answer
  • Leverage your soft skills and personality to stand out

Possible answer to “What can you contribute to this company?”

“In my last role, I successfully transformed our team’s operations with the implementation of [technology product]. As a result, our productivity jumped by almost 40%. I am always looking for ways to improve and learn something new. I hope I could bring that energy to your team and find new improvements for us. I’m excited to learn more from you about how I can improve in this role.”

Read More: How To Answer “What Can You Contribute To This Company?”

9. Why do you want to work at this company?

This is where your in-depth company research is going to shine! When you are conducting research on the company, this should be one of the main questions you are looking to answer. As a result, ask yourself the following during your research:

  • What do I like most about this business?
  • Do the company’s mission and values speak to me?
  • How does this company make an impact, and what do I like about that?
  • What can you learn about the company or team’s operations that excites you?

Possible answer to “Why do you want to work at this company?”

“I always knew that I wanted to work in this industry because I truly believe that the impact you make is so important. However, your mission goes beyond that and really speaks to how I view my job. I can also see that your organization is growing rapidly, and I am always looking to step up into new challenges. It seems like your department in particular leads the charge on that growth, and I’m excited to be at the forefront of that change.”

10. Why do you want this job?

Similar to the above question, your answer should be specific to the company and the role. What stands out about this job from all the other jobs out there? Ask yourself:

  • What skills do I bring to the table?
  • How can I grow in this role?
  • How can I make an impact?
  • What is most exciting about this job?
  • What do I want most in my next job?
  • What do I like about the company?

Possible answer to “Why do you want this job?”

“Aside from really identifying with [Company]’s mission, I know that I can add to that impact in this role. As I am leaving my current job, I am looking for a strong team to collaborate with and learn from, as well as opportunities for growth. I’m excited by the idea that I could eventually [XYZ] in this role, and I know that my skills in [ABC] can help us increase our impact as a team.”

11. Why should we hire you?

Now, that’s an intimidating (and tricky) interview question. However, this is your straightforward opportunity to sell yourself to this hiring manager! In your answer, you should:

  • Sell your experience
  • Explain how you can add to the culture
  • Show why you are better than other candidates

Possible answer to “Why should we hire you?”

“I know from my experience in this field that it can be challenging to find someone who can step up to the plate by both planning and executing in this type of role. However, my experience has allowed me to grow in both of these areas, with over 7 years dedicated to understanding the execution of this responsibility. After I understood the machinations of that, my role at [previous company] allowed me to plan each step of the process from A to Z. With that experience, I feel confident that I can not only manage this team effectively, but increase collaboration and retention through my management techniques. I have such a niche background with my experience at [company] doing [skill] that I think it really makes me a unique fit for this role. I certainly hope that I could make a positive impact on your team.”

12. Sell me this pen.

If you’re in a sales career, you may be put on the spot to sell something in front of you. What the hiring manager is looking for is:

  • Your ability to sell under pressure
  • Your confidence and charisma
  • How you can make a connection with a buyer

Possible answer to “Sell me this pen.”

“My mom always used to tell me that I shouldn’t worry about the little things in life. And, of course, she was right. It might be an extreme example, but those little things that you stress over: what to wear, which route to take to work, what to write with—they add up. And when you hardly have time for lunch, the last thing you need to worry about is whether you brought a pen into the meeting. The unique features of this pen, from the pocket clip to the small magnet, to the unique ink used, are all designed so that you don’t have to worry about pens. It may not be something you think about often until you don’t have one. In using these pens myself, I keep one in every room, and I even got my mom to switch to them as well—she keeps one on the refrigerator to write down reminders. And after a year, it still hasn’t run out of ink! With our deal happening today, you can get a second pack for free when you order the first. Can I put you down for your first order?”

13. What is your work style?

It’s not too difficult to imagine what your interviewer is trying to learn with this question. Not only do they want to understand how you might fit into this role and their team, but they also might want to know how you prefer to work so they can better manage you. To answer this, think about:

  • How you like to collaborate with team members
  • How and when you do your best work
  • How you organize and structure your day

Possible answer to “What is your work style?

“I find that my organizational tools are the key to my success. I usually manage all of my tasks within a platform where I can track everything, and make sure I don’t let anything drop. I’ve worked on teams where we all use these platforms, which can be a fun way to collaborate! In terms of getting work done, I like to set aside blocks of time for focused work and research, and I love coming together with my team for brainstorming sessions. I always find new, exciting ideas in that type of environment. Lastly, I appreciate when context is given for the projects I’m working on, as I find that it helps me prioritize my tasks.”

14. What is your management style?

This can be difficult to put your finger on; one manager never matches another in their style. However, you can articulate your answer by asking yourself questions like:

  • How do you set goals for direct reports?
  • How do you motivate employees?
  • How do you explain projects or tasks?
  • How do you provide learning and growth opportunities?

Possible answer to “What is your management style?”

“I tend to find that my management style is dictated by the individual. I have to learn how they communicate, how they internalize information, and what specifically motivates them. One employee may learn by diving in and doing something themselves, while another may learn by watching. One thing I am always sure to do is to give full context into the tasks I’m asking them to handle. I find this helps with motivation and to show their overall impact. Lastly, I think trust is critical to a functional manager/employee relationship. Without trusting each other, we’re not likely to succeed together.”

Read More: How To Answer “What Is Your Management Style?”

15. What is your greatest strength?

Employers will ask “what is your greatest strength?” to identify whether your abilities match up with their requirements. They want to know if you feel confident, you can do the job, and you’d be a great addition to the team. As a result, this question is a great opportunity to show a hiring manager why you’d be a great fit! Answer by:

  • Identifying your top strengths
  • Focusing on how those strengths are great for the role
  • Backing this up with a story

Possible answer to “What is your greatest strength?”

“I think one of my best qualities is clear communication. When I interact with clients at [Company], I am often dealing with people in [industry] who don’t necessarily speak the same language that we do. However, I can identify their struggle and articulate it back to them in a way that we both understand. I can also explain solutions in simple ways that make it easy for them to grasp the value of our products. For example, I once worked with a client who struggled with [XYZ]. They were not an expert in that and had trouble properly explaining their problem. However, I was able to pick up on it and show them exactly how we could help. They are still a client today, and throughout the years, I’ve acted as a valuable resource to them, which continues to show my expertise in the field. I think this type of communication skill is exactly what you’re looking for in this role, which is why I’m so excited about this opportunity.”

Read More: How To Answer “What Is Your Greatest Strength?”

16. What is your biggest weakness?

If you’ve never been asked this question during a job interview before, you’re likely in the minority of working professionals. For many, discussing your weaknesses during a job interview is an expectation and something you should prepare for in the lead-up to the interview. While nobody likes to admit what makes them less than perfect, you can use this opportunity to your advantage and present yourself as the best possible person for the position! To answer this, try the following:

  • Don’t try a cop out answer like “I’m a perfectionist”
  • Be honest about your flaws
  • Avoid technical answers like “I’m not great with Excel”
  • Say what you’re doing to improve

Possible answer to “What is your biggest weakness?”

“I sometimes struggle with multitasking because I have difficulty staying organized. However, I’ve been working to improve upon this by writing down what tasks I need to accomplish, and then prioritizing them by their deadline.”

Read More: How To Effectively Address Weaknesses During A Job Interview

17. How do you handle conflict in the workplace?

Since conflict can come into play in a variety of situations at work, employers love to ask questions about conflict in the workplace to evaluate your interpersonal skills. In your answer, you should be able to explain:

  • How you process your thoughts
  • A willingness to listen without judgment
  • Your ability to remain professional

Possible answer to “How do you handle conflict in the workplace?”

“When I have a disagreement with someone, my first step is to listen to their argument. I always go in with the idea that I might be missing something that is key to understanding. If I still disagree with them, I try to think about all of my reasons for my perspective and present them as clearly as possible. At the end of the day, I always remain professional and defer to leadership to make a decision.”

Read More: Answering: “How Do You Handle Conflict In The Workplace?”

18. What is your dream job?

The key to preparing a successful answer to this question is to understand why an employer is asking it in the first place. They want to understand your skillset, level of motivation, values, and overall interests. The hiring manager doesn’t need you to repeat their job description back to them, but they’d like to see that you are the right fit. When in doubt, you can use your goals and ambitions as a starting place, and connect why this job will help you get there.

Possible answer to “What is your dream job?”

“While I’m not sure what my end goal in my career is, I do know that I want to be at the forefront of the design field. When I think about what I need to do to get there, I know I have a lot to learn before I could be a leader in this space. But this opportunity at [Company] can certainly get me closer to that dream. As leaders in design technology, I know that I will gain so much out of this experience, and I’m really motivated to make a meaningful contribution here.”

Read More: How To Answer: What Is Your Dream Job?

19. Where do you see yourself in 5 years?

A similarly agonizing question to the previous one; you’re not a fortune teller after all. Ultimately, this is an opportunity to think about the next steps in your career. One or two turns down the road, where would you like to be? It’s also okay if you’re not sure—simply express that this role could be an important step to helping you figure out what it is that you want for your career.

Possible answer to “Where do you see yourself in 5 years?”

“What I’m most excited about in this role is learning from your team, as I am coming from a smaller operation. In five years, I would hope that I have a better understanding of how a large team operates and that I can contribute effectively in multiple areas. I would also love to grow into a leadership role and help others grow as well.”

Read more: How To Answer: Where Do You See Yourself In 5 Years?

20. Are you interviewing with any other companies?

This is a tricky interview question to answer because you have to strike the right balance. On the one hand, you want the hiring manager to know that you are talented and in-demand, but you also don’t want to seem blasé about this opportunity. You also don’t want to show your hand if you’re not in any other interview processes. Overall, honestly is the best policy here, but you don’t have to give it all away.

Possible answer to “Are you interviewing with any other companies?”

“I’m currently in other interview processes, all at different stages. Each role has something unique to offer, but I love the growth opportunities that exist here, so I’m excited about continuing the process.”

Or…

“I’ve just started my job search process, so I’ve had a couple of introductory conversations so far. I’m most intrigued by this role and the opportunity to make such a powerful impact.”

Hint: If you have other offers on the table, let them know. This will get the employer to move faster and make a more competitive offer.

21. When can you start?

This question is less tricky than it sounds! What is important to remember is that you should be realistic about what you can promise. Additionally, you want to consider showing respect to your current employer, which the hiring manager will appreciate. If you don’t have any commitments to a current employer, let them know so you can start sooner!

Possible answer to “When can you start?”

“I want to be as respectful as possible to my current employer, and I have a lot of responsibility in my current role, so, if possible, I would like to give four weeks’ notice upon my acceptance of an offer. Would a start date on [date] work for you?”

Read more: How To Answer: When Can You Start?

22. Do you have any questions for us?

Remember, an interview is a two-way street. However, many job seekers do not take advantage of this opportunity. If you don’t ask questions when given the chance, this tells the employer that you:

  • Are not interested in the role
  • Lack curiosity about the company and role
  • Didn’t do your research
  • Don’t know what you want from this role

Possible question topics you can ask about:

When you are presented the opportunity to ask questions, consider asking about:

  • The role
  • The team
  • The culture
  • Opportunities for growth
  • The company

Read More: [Infographic] 15 Questions That Will Help You Stand Out In An Interview

23. What are your salary expectations?

At the heart of any interview process comes the time to discuss the big ‘S’ word: salary. Whether you’re confident in your negotiation skills or not, beginning the conversation with a hiring manager about salary expectations can be a tricky one. To answer this, it is good to start by:

  • Doing your own market research
  • Asking what the salary range is for this position
  • Asking about the total compensation package
  • Giving a salary range you are comfortable in (keep in mind, they may present an offer at the lower end, so be strategic about the range you give)

Possible answer to “What are your salary expectations?”

“Taking my experience level into account, as well as your budget for this role and what I understand to be the market value of this position, I would be looking for a salary range between $80,000 and $85,000. I would also love to learn about other elements of your compensation and benefits packages to take the full compensation value into consideration.”

Read More: The Dos and Don’ts of Answering “What is Your Target Salary?”

24. What is your current salary?

This question, while not illegal everywhere in the U.S., is illegal in several states across the country because it perpetuates a cycle of underpaying workers rather than paying for the skillset required to do the job. Regardless of whether this question is legal in your state, you do not have to answer it. If it is asked, deflect by giving your target salary range.

Possible answer to “What is your current salary?”

“Well, my target salary for my next position is around $60,000 to $65,000.”

25. Are you planning to have children?

Keep in mind, this question, along with any questions about race, ethnicity, citizenship status, country of origin, religion, gender, sexual orientation, or marital/family status are illegal. However, the question still gets asked—and often (many times by accident). So, how do you handle this? Try to keep your answer brief and vague, before steering back into the job and company.

Possible answer to “Are you planning to have children?”

“I really try to keep my work and personal life separate. But, I would love to discuss more about this role. Can you tell me what I can expect to accomplish in the first six months here?”

Subscribe to the Tandym blog

Get our latest job search and career insights delivered straight to your inbox

Related Resources